1-Bromo-4-nitrobenzene → (E)-3-Cyclohexyl-2-(4-nitro-phenyl)-prop-2-en-1-ol

HRID 2103641Notes

Reaction equation

HRID 2103641 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH:11]1(/[CH:17]=[C:18](\B2OC(C)(C)C(C)(C)O2)/[CH2:19][OH:20])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.[F-].[Cs+]>O1CCOCC1.C(OCC)(=O)C.C1(P([Pd-4](P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH:11]1(/[CH:17]=[C:18](\[C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)/[CH2:19][OH:20])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

7

Reactant 3

HCID 114661-Bromo-4-nitrobenzeneHCID 25953Cesium fluorideHCID 67084598(E)-3-cyclohexyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-prop-2-en-1-ol

Product 1

HCID 67084428(E)-3-Cyclohexyl-2-(4-nitro-phenyl)-prop-2-en-1-olYield 68.2%

Reagents, catalysts & solvents 3

HCID 178420553HCID 178420553, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

Add tetrakis(triphenylphosphino)palladium(0) (0.60 g, 0.52 mmol) to a solution of 1-bromo-4-nitro-benzene (0.76 g, 3.76 mmol) and (E)-3-cyclohexyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-prop-2-en-1-ol (1.13 g, 4.24 mmol) in dioxane (20 mL). Add cesium fluoride (1.75 g, 12 mmol) and stir the reaction mixture for 12 h at 80° C. Allow the reaction mixture to cool to r.t. Dilute the reaction mixture with ethyl acetate and wash with water. Separate the layers. Dry the organic phase over sodium sulfate, filter and concentrate. Purify the residue via silica gel chromatography, eluting with a gradient from 95:5 to 7:3 hexanes:ethyl acetate to obtain the title compound (0.67 g). 1H-NMR (CDCl3) δ=1.05-1.72 (m, 10 H), 1.89-2.04 (m, 1H), 4.28-4.36 (m, 2H), 5.61-5.69 (m, 1H), 7.34-7.43 (m, 2H), 8.18-8.26 (m, 2H).

Workup

  1. washwash with water
  2. customSeparate the layers
  3. dry with materialDry the organic phase over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify the residue via silica gel chromatography
  7. washeluting with a gradient from 95:5 to 7:3 hexanes

Sources & evidence

ORD record
ord-1af79803a3204b4fb639cc0c29c6849b
Source dataset
uspto-grants-2009_08
Patent number
US07576108B2

Reaction notes

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